25CN-NBOH hydrochloride
25CN-NBOH hydrochloride exhibits agonist activity at the 5-HT2a receptor, shows 90- to 100-fold selectivity over the 5-HT2c receptor, and possesses blood-brain barrier permeability. 25CN-NBOH hydrochloride acts as an interoceptive agent with partial agonist-like properties. 25CN-NBOH hydrochloride serves as a pharmacological tool for 5-HT2A receptor research, and its tritiated form functions as a selective agonist radioligand. 25CN-NBOH hydrochloride can be used to investigate diseases characterized by cognitive rigidity, schizophrenia, obsessive-compulsive disorder, depression, pain, inflammation, migraine, and cluster headache.
For research use only. We do not sell to patients.
- CAS No.: 1539266-32-4
- Formula: C18H21ClN2O3
- Molecular Weight:348.82
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
All 5-HT Receptor Isoforms
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Biological Activity
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Human 5-HT2A Receptor 2.1 nM (EC50) |
Human 5-HT2C Receptor 132 nM (EC50) |
Human 5-HT2A Receptor 8.62 (pEC50) |
Human 5-HT2C Receptor 6.45 (pEC50) |
25CN-NBOH hydrochloride (2 h) is a high-affinity ligand for human 5-HT2AR (Ki = 1.7 nM). In a [3H]Cimbi-36 competitive binding assay using membranes from tsA201 cells transfected with human receptors, 25CN-NBOH shows 76-fold selectivity for human 5-HT2AR over human 5-HT2CR[1].
25CN-NBOH hydrochloride (1 h) is a potent partial agonist of human 5-HT2AR (EC50 = 2.4 nM, achieving 77% of the maximal response induced by 5-HT), while acting as a full agonist of human 5-HT2CR (EC50 = 46 nM, achieving 119% of the maximal response induced by 5-HT), as determined by an IP-One HTRF assay using stable HEK293 cell lines[1].
25CN-NBOH hydrochloride (30 min) is a potent partial agonist of human 5-HT2AR (EC50 = 0.41 nM, achieving 80% of the maximal effect of 5-HT). It also acts as a partial agonist of human 5-HT2CR (EC50 = 5.8 nM, achieving 56% of the maximal effect of 5-HT) in a Ca2+/Fluo-4 assay using stable HEK293 cell lines[1].
25CN-NBOH hydrochloride exhibits high in vitro binding selectivity for 5-HT2AR, with 52-100-fold higher affinity for 5-HT2AR than for 5-HT2CR, 37-fold higher affinity than for 5-HT2BR, and acts as a potent agonist of 5-HT2AR[2].
25CN-NBOH hydrochloride shows 100-fold binding selectivity for human 5-HT2AR over rat 5-HT2CR, with a Ki value of 1.3 nM for human 5-HT2AR and 132 nM for rat 5-HT2CR[3].
25CN-NBOH hydrochloride (30 min) is a potent agonist with 90-fold functional selectivity for human 5-HT2AR over human 5-HT2CR. The EC50 values are 2.1 nM for human 5-HT2AR and 190 nM for human 5-HT2CR[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
25CN-NBOH (0.3-10 mg/kg; i.p.) hydrochloride reduces activity in female NMRI mice in an anxiety-related marble burying assay at doses of 0.3, 1, 3, and 10 mg/kg (i.p.)[1].
25CN-NBOH (0.3-30 mg/kg; i.p.; single dose) hydrochloride induces 5-HT2A receptor-mediated head twitch behavior in Mus musculus, with a maximal response of ~10 head twitches at 1.0 mg/kg, and dose-dependently attenuates DOI-elicited head twitches at doses ≥3.0 mg/kg[2].
25CN-NBOH (0.1-30 mg/kg; i.p.; cumulative dose) hydrochloride produces partial 5-HT2A receptor-mediated generalization to the DOI discriminative cue in mice, reaching a maximum of 55% DOI-appropriate responding at cumulative doses of 10.0 and 30.0 mg/kg[2].
25CN-NBOH (0.1-30 mg/kg; i.p.; cumulative dose) hydrochloride does not generalize to the M100907 discriminative cue in mice, demonstrating no antagonist-like interoceptive effects at 5-HT2A receptors[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6J (male, 6-8 weeks old)[1]
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Dosage:0.51 mg/kg
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Administration:i.p.
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Result:Induced head-twitch response with an ED50 of 1.45 μM/kg.
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Animal Model:NMRI (female, 7-13 weeks old)[1]
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Dosage:0.3 mg/kg; 1 mg/kg; 3 mg/kg; 10 mg/kg
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Administration:i.p.
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Result:Mediated robust reductions in mouse activity in the anxiety-related marble burying assay at doses of 0.3, 1, 3, and 10 mg/kg.
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Animal Model:NIH Swiss (male, 20-25g on delivery)[2]
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Dosage:0.3 mg/kg; 1.0 mg/kg; 3.0 mg/kg; 10.0 mg/kg; 30.0 mg/kg
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Administration:i.p.; single dose
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Result:Elicited significantly more head twitches than saline at 1.0 and 3.0 mg/kg, with a maximum response of ~10 head twitches at 1.0 mg/kg.
Significantly attenuated head twitches elicited by 1.0 mg/kg 25CN-NBOH after pretreatment with M100907.
Did not alter head twitches elicited by 30.0 mg/kg 25CN-NBOH after pretreatment with RS102221.
Dose-dependently suppressed DOI-elicited head twitches at 3.0, 10.0, and 30.0 mg/kg, with 30.0 mg/kg reducing responses to levels significantly lower than all lower doses.
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Animal Model:NIH Swiss (male, food-restricted to 30g during testing)[2]
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Dosage:0.1 mg/kg; 0.3 mg/kg; 1.0 mg/kg; 3.0 mg/kg; 10.0 mg/kg; 30.0 mg/kg
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Administration:i.p.; cumulative dose
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Result:Produced partial generalization to the DOI training cue, eliciting a maximum of 55% DOI-appropriate responding at 10.0 and 30.0 mg/kg, which was significantly more than saline but significantly less than the DOI training dose.
Shifted the dose-effect curve for DOI-like interoceptive effects rightward after pretreatment with M100907, with no statistical significance reached at any dose.
Suppressed response rates at the highest cumulative dose, with 3/6 mice failing to complete the fixed-ratio 5 requirement.\nDid not generalize to the M100907 training cue, eliciting only saline-like responding across all cumulative doses tested.
Produced significantly less M100907-appropriate responding than the M100907 training dose at all doses.
Suppressed response rates at the highest cumulative dose.
Chemical Information
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CAS No. 1539266-32-4
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Molecular Weight 348.82
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Formula C18H21ClN2O3
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SMILES
N#CC1=C(OC)C=C(CCNCC2=C(O)C=CC=C2)C(OC)=C1.Cl
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[2]. Fantegrossi WE, et al. Hallucinogen-like effects of 2-([2-(4-cyano-2,5-dimethoxyphenyl) ethylamino]methyl)phenol (25CN-NBOH), a novel N-benzylphenethylamine with 100-fold selectivity for 5-HT₂A receptors, in mice. Psychopharmacology (Berl). 2015 Mar;232(6):1039-47. [Content Brief]
[3]. Hansen M, et al. Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chem Neurosci. 2014 Mar 19;5(3):243-9. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)